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Perylene

Drugs and Chemicals · NLM MeSH · updated 2026-10-31 · version 1

Citations verified against PubMedNot yet clinician-reviewed10 referencesApproximately 4 min read

A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene.

Table of Contents

1. Definition2. Research landscape3. Reading the evidence4. Open-access studies5. Key reviews6. References7. About this article

Definition and research guide

This page combines a MeSH definition, publication statistics and selected research abstracts. It is a starting point for reading the literature, not a medical textbook or a systematic evidence review.

Content available: 4 complete abstracts (805 words), 10 references. Full article text is not stored or reproduced here; follow the PMID, DOI or PMC links to read the original sources and their access terms.

Definition

A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.

Definition: NLM Medical Subject Headings (MeSH) scope note (Public domain (U.S. National Library of Medicine); attribution requested). View the MeSH record.

Also known as: Perilene; Peri-Dinaphthalene; Peri Dinaphthalene.

Where it fits in the MeSH classification

Broader topics
Anthracenes; Phenalenes

Research landscape

PubMed indexes 2,892 records tagged with the MeSH heading “Perylene” (counts retrieved 2026-10-31). 611 of them (21.1%) were published from 2020 onward, and the busiest period so far is 2010-2019 with 1,111 records.

Reviews account for 125 records (4.3%) and meta-analyses for 4. Randomized controlled trials number 26 (0.9%) as a share of all records on the topic. Randomized trials make up only a small share of this literature, so much of what is known comes from laboratory, observational or descriptive work.

PubMed records by publication periodthrough 1999: 339 records; 2000-2009: 831 records; 2010-2019: 1,111 records; 2020 onward: 611 records339through 19998312000-20091,1112010-20196112020 onward
Records in PubMed indexed with this heading, by publication period. Real counts from NCBI E-utilities; the final period covers only part of the current year. Volume reflects how much has been published, not how strong the evidence is.
Show the data
PeriodRecords
through 1999339
2000-2009831
2010-20191,111
2020 onward611
Share of records by publication typeReviews: 4.3 percent; Meta-analyses: 0.1 percent; Randomized controlled trials: 0.9 percentReviews4.3% (125)Meta-analyses0.1% (4)Randomized controlled trials0.9% (26)
Share of all PubMed records on this heading that carry each publication type. Types overlap with other records, so the shares do not sum to 100%.
Publication-type chart data
Publication types among 2,892 PubMed records
TypeRecordsShare
Reviews1254.3%
Meta-analyses40.1%
Randomized controlled trials260.9%

Method: PubMed query "Perylene"[MeSH Terms] with publication-type and date filters, retrieved 2026-10-31.

Reading the evidence in drugs and chemicals

Studies of a chemical or drug can answer very different questions: what it is and how it behaves in cells and animals, how the body handles it, and whether it changes outcomes in people. Laboratory and animal findings often do not carry over to patients, and observational studies of exposures are confounded by who uses a substance and why. Nothing on this page is a recommendation to use, avoid, start or stop any substance or medicine; talk to a qualified clinician or pharmacist about your own situation. Check the dose, the species, the comparison group and whether a patient-relevant outcome was measured.

Evidence from open-access studies

These open-access studies come from PubMed’s best-match results for this heading (papers whose main topic it is), ranked here by citation count, with one recent addition. Each abstract is reproduced in full under its recorded open licence so that you can read the authors’ own words. They illustrate the literature; they are not a systematic summary of it. Citation counts measure attention, not reliability or clinical benefit.

Study comparison — selected abstracts, not a systematic review
Study / authorsYearSource label / designEurope PMC citationsLicence / source
Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells
Zhong Y, Trinh MT, Chen R, Purdum GE, Khlyabich PP, Sezen M, et al.
2015Research article
Design not recorded in structured metadata
202cc by
PMID 26382113 · DOI · PMC4595599
Non-contact identification and differentiation of illicit drugs using fluorescent films
Liu K, Shang C, Wang Z, Qi Y, Miao R, Liu K, et al.
2018Research article
Design not recorded in structured metadata
87cc by
PMID 29703929 · DOI · PMC5923207
The diverse roles of glutathione-associated cell resistance against hypericin photodynamic therapy
Theodossiou TA, Olsen CE, Jonsson M, Kubin A, Hothersall JS, Berg K
2017Research article
Design not recorded in structured metadata
74cc by
PMID 28254657 · DOI · PMC5333531
Method for Isolating Hypericin from Hypericum perforatum and Preparing Its Micelles for Biomedical Applications
Medvedev D, Dalinina V, Golik P, Lavrinova P, Plotnikova E, Usachev M, et al.
2026Research article
Design not recorded in structured metadata
0cc by
PMID 42357446 · DOI · PMC13305305

Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells [1]

Research article Zhong Y, Trinh MT, Chen R, Purdum GE, Khlyabich PP, Sezen M, et al. · · 2015 · cited 202 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
Despite numerous organic semiconducting materials synthesized for organic photovoltaics in the past decade, fullerenes are widely used as electron acceptors in highly efficient bulk-heterojunction solar cells.
Closing excerpt
This study describes a new motif for designing highly efficient acceptors for organic solar cells.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (150 words)

Despite numerous organic semiconducting materials synthesized for organic photovoltaics in the past decade, fullerenes are widely used as electron acceptors in highly efficient bulk-heterojunction solar cells. None of the non-fullerene bulk heterojunction solar cells have achieved efficiencies as high as fullerene-based solar cells. Design principles for fullerene-free acceptors remain unclear in the field. Here we report examples of helical molecular semiconductors as electron acceptors that are on par with fullerene derivatives in efficient solar cells. We achieved an 8.3% power conversion efficiency in a solar cell, which is a record high for non-fullerene bulk heterojunctions. Femtosecond transient absorption spectroscopy revealed both electron and hole transfer processes at the donor-acceptor interfaces. Atomic force microscopy reveals a mesh-like network of acceptors with pores that are tens of nanometres in diameter for efficient exciton separation and charge transport. This study describes a new motif for designing highly efficient acceptors for organic solar cells.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 26382113 · DOI · PMC4595599

Non-contact identification and differentiation of illicit drugs using fluorescent films [2]

Research article Liu K, Shang C, Wang Z, Qi Y, Miao R, Liu K, et al. · · 2018 · cited 87 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
Sensitive and rapid identification of illicit drugs in a non-contact mode remains a challenge for years.
Closing excerpt
Based upon the discoveries, a conceptual, two-sensor based detector is developed, and non-contact detection of the drugs is realized.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (161 words)

Sensitive and rapid identification of illicit drugs in a non-contact mode remains a challenge for years. Here we report three film-based fluorescent sensors showing unprecedented sensitivity, selectivity, and response speed to the existence of six widely abused illicit drugs, including methamphetamine (MAPA), ecstasy, magu, caffeine, phenobarbital (PB), and ketamine in vapor phase. Importantly, for these drugs, the sensing can be successfully performed after 5.0 × 105, 4.0 × 105, 2.0 × 105, 1.0 × 105, 4.0 × 104, and 2.0 × 102 times dilution of their saturated vapor with air at room temperature, respectively. Also, presence of odorous substances (toiletries, fruits, dirty clothes, etc.), water, and amido-bond-containing organic compounds (typical organic amines, legal drugs, and different amino acids) shows little effect upon the sensing. More importantly, discrimination and identification of them can be realized by using the sensors in an array way. Based upon the discoveries, a conceptual, two-sensor based detector is developed, and non-contact detection of the drugs is realized.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 29703929 · DOI · PMC5923207

The diverse roles of glutathione-associated cell resistance against hypericin photodynamic therapy [3]

Research article Theodossiou TA, Olsen CE, Jonsson M, Kubin A, Hothersall JS, Berg K · · 2017 · cited 74 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
The diverse responses of different cancers to treatments such as photodynamic therapy of cancer (PDT) have fueled a growing need for reliable predictive markers for treatment outcome.
Closing excerpt
As a conclusion we have herein shown that the different GSH based cell defense mechanisms can be utilized as predictive markers for the outcome of PDT and as a guide for selecting optimal combination strategies.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (300 words)

The diverse responses of different cancers to treatments such as photodynamic therapy of cancer (PDT) have fueled a growing need for reliable predictive markers for treatment outcome. In the present work we have studied the differential response of two phenotypically and genotypically different breast adenocarcinoma cell lines, MCF7 and MDA-MB-231, to hypericin PDT (HYP-PDT). MDA-MB-231 cells were 70% more sensitive to HYP PDT than MCF7 cells at LD50. MCF7 were found to express a substantially higher level of glutathione peroxidase (GPX4) than MDA-MB-231, while MDA-MB-231 differentially expressed glutathione-S-transferase (GSTP1), mainly used for xenobiotic detoxification. Eighty % reduction of intracellular glutathione (GSH) by buthionine sulfoximine (BSO), largely enhanced the sensitivity of the GSTP1 expressing MDA-MB-231 cells to HYP-PDT, but not in MCF7 cells. Further inhibition of the GSH reduction however by carmustine (BCNU) resulted in an enhanced sensitivity of MCF7 to HYP-PDT. HYP loading studies suggested that HYP can be a substrate of GSTP for GSH conjugation as BSO enhanced the cellular HYP accumulation by 20% in MDA-MB-231 cells, but not in MCF7 cells. Studies in solutions showed that L-cysteine can bind the GSTP substrate CDNB in the absence of GSTP. This means that the GSTP-lacking MCF7 may use L-cysteine for xenobiotic detoxification, especially during GSH synthesis inhibition, which leads to L-cysteine build-up. This was confirmed by the lowered accumulation of HYP in both cell lines in the presence of BSO and the L-cysteine source NAC. NAC reduced the sensitivity of MCF7, but not MDA-MB-231, cells to HYP PDT which is in accordance with the antioxidant effects of L-cysteine and its potential as a GSTP substrate. As a conclusion we have herein shown that the different GSH based cell defense mechanisms can be utilized as predictive markers for the outcome of PDT and as a guide for selecting optimal combination strategies.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 28254657 · DOI · PMC5333531

Method for Isolating Hypericin from Hypericum perforatum and Preparing Its Micelles for Biomedical Applications [4]

Research article Medvedev D, Dalinina V, Golik P, Lavrinova P, Plotnikova E, Usachev M, et al. · · 2026

Abstract reading summary — source excerpts
Opening excerpt
Hypericin (Hyp) is a naturally occurring photosensitizer (PS) exhibiting a broad spectrum of biological activities.
Closing excerpt
The proposed method enables the production of a stable Hyp formulation that retains its photosensitizing properties, thereby opening promising avenues for its application in photodynamic and sonodynamic therapies.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (194 words)

Hypericin (Hyp) is a naturally occurring photosensitizer (PS) exhibiting a broad spectrum of biological activities. However, its high hydrophobicity significantly limits its medical applicability. This study aimed to develop an efficient method for extracting Hyp from Hypericum perforatum L. biomass and to obtain its water-soluble micellar formulation. A protocol for Hyp isolation from the aerial parts of the plant was established, involving a preliminary defatting step using a Soxhlet apparatus, followed by ultrasonic-assisted extraction with acetone. The water-soluble formulation was prepared via the thin-film hydration method using the nonionic block copolymer Pluronic F-127. The resulting micelles demonstrated colloidal stability, with a mean hydrodynamic diameter of approximately 30 nm. A high Hyp loading efficiency was achieved, with an encapsulation efficiency (EE) of 95.4 ± 2.7%, yielding a concentration of 600.6 ± 16.6 µM within the micellar formulation. In vitro biological studies were performed using the murine GL261 glioblastoma cell line. The micellar Hyp formulation exhibited efficient time-dependent cellular accumulation and photoinduced cytotoxicity, with no observable dark toxicity. The proposed method enables the production of a stable Hyp formulation that retains its photosensitizing properties, thereby opening promising avenues for its application in photodynamic and sonodynamic therapies.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 42357446 · DOI · PMC13305305

Key reviews and meta-analyses

The most cited review-type papers among PubMed’s best-match results for this heading, listed with bibliographic details only. Follow the links for the full text and access terms.

  • Research article St John's wort for depression--an overview and meta-analysis of randomised clinical trials [5]
    Linde K, Ramirez G, Mulrow CD, Pauls A, Weidenhammer W, Melchart D · BMJ · 1996 · cited 462 times (Europe PMC)
  • Research article Perylene imides for organic photovoltaics: yesterday, today, and tomorrow [6]
    Li C, Wonneberger H · Adv Mater · 2012 · cited 359 times (Europe PMC)
  • Research article Hypericin in cancer treatment: more light on the way [7]
    Agostinis P, Vantieghem A, Merlevede W, de Witte PA · Int J Biochem Cell Biol · 2002 · cited 275 times (Europe PMC)
  • Research article Molecular assemblies of perylene bisimide dyes in water [8]
    Görl D, Zhang X, Würthner F · Angew Chem Int Ed Engl · 2012 · cited 242 times (Europe PMC)
  • Research article Hypericins as potential leads for new therapeutics [9]
    Karioti A, Bilia AR · Int J Mol Sci · 2010 · cited 171 times (Europe PMC)
  • Research article Novel therapeutic and diagnostic applications of hypocrellins and hypericins [10]
    Diwu Z · Photochem Photobiol · 1995 · cited 166 times (Europe PMC)

References

  1. Zhong Y, Trinh MT, Chen R, Purdum GE, Khlyabich PP, Sezen M, et al.. Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells. . 2015. PMID 26382113 · DOI · PMC4595599
  2. Liu K, Shang C, Wang Z, Qi Y, Miao R, Liu K, et al.. Non-contact identification and differentiation of illicit drugs using fluorescent films. . 2018. PMID 29703929 · DOI · PMC5923207
  3. Theodossiou TA, Olsen CE, Jonsson M, Kubin A, Hothersall JS, Berg K. The diverse roles of glutathione-associated cell resistance against hypericin photodynamic therapy. . 2017. PMID 28254657 · DOI · PMC5333531
  4. Medvedev D, Dalinina V, Golik P, Lavrinova P, Plotnikova E, Usachev M, et al.. Method for Isolating Hypericin from Hypericum perforatum and Preparing Its Micelles for Biomedical Applications. . 2026. PMID 42357446 · DOI · PMC13305305
  5. Linde K, Ramirez G, Mulrow CD, Pauls A, Weidenhammer W, Melchart D. St John's wort for depression--an overview and meta-analysis of randomised clinical trials. BMJ. 1996. PMID 8704532 · DOI · PMC2351679
  6. Li C, Wonneberger H. Perylene imides for organic photovoltaics: yesterday, today, and tomorrow. Adv Mater. 2012. PMID 22228467 · DOI
  7. Agostinis P, Vantieghem A, Merlevede W, de Witte PA. Hypericin in cancer treatment: more light on the way. Int J Biochem Cell Biol. 2002. PMID 11849990 · DOI
  8. Görl D, Zhang X, Würthner F. Molecular assemblies of perylene bisimide dyes in water. Angew Chem Int Ed Engl. 2012. PMID 22573415 · DOI
  9. Karioti A, Bilia AR. Hypericins as potential leads for new therapeutics. Int J Mol Sci. 2010. PMID 20386655 · DOI · PMC2852855
  10. Diwu Z. Novel therapeutic and diagnostic applications of hypocrellins and hypericins. Photochem Photobiol. 1995. PMID 7568399 · DOI

About this article

Sources
NLM Medical Subject Headings (definition, synonyms); NCBI PubMed (counts, identifiers); Europe PMC (open-access abstracts and citation counts).
Verification
Every reference was resolved against PubMed on 2026-10-31; title, year and DOI matched.
Review state
automated source verified; no human expert review has been recorded yet.
Version
1, last updated 2026-10-31.

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At a glance

2,892
PubMed records on this heading
21%
published since 2020
125
review articles
26
randomized trials
10
verified references below

Counts come from PubMed on 2026-10-31; they show how much has been written, not how strong the evidence is.

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